Morpholine → 3,4-Dihydro-1,4-dimethyl-2[2-(4-morpholinyl)ethyl]-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

HRID 1031178Notes

Reaction equation

HRID 1031178 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[N:17]([CH3:18])[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5]1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:18][N:17]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5][CH:4]1[CH2:3][CH2:2][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 198197592-(2-Chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

Product 1

HCID 198197743,4-Dihydro-1,4-dimethyl-2[2-(4-morpholinyl)ethyl]-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

Conditions

Temperature
60 °C

Procedure

To 3.0 g (0.0103 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one was added 20 mL of morpholine. The mixture was stirred at 60° C. for 4 hr. The morpholine was removed at 60° C. and approximately 1 mm Hg. The residue was partitioned between 100 mL of CH2Cl2 and 100 mL of 1N NaOH. The basic layer was reextracted with 50 mL of CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was crystallized from isopropyl alcohol to afford 2.1 g (59%) of white analytically pure crystals, mp 149°-151.5° C.

Workup

  1. customThe morpholine was removed at 60° C.
  2. customThe residue was partitioned between 100 mL of CH2Cl2 and 100 mL of 1N NaOH
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was crystallized from isopropyl alcohol
  7. customto afford 2.1 g (59%) of white analytically pure crystals, mp 149°-151.5° C.

Sources & evidence

ORD record
ord-75ec29a1399f4ce6998dc52c12adc171
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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